Where Trouble Leads Us
by icecreampie
Summary: Crossover: Supernatural Gossip Girl One Tree Hill. Blair/Dean. Blair and Dean are long lost family friends. Fate brings them together with their own cupid, Jamie Scott in their summer holidays. Starts off a bit serious, then later promised to be lighter.


**Where Trouble Leads Us To**

**Chapter 1 – Beginning in the End.**

**What happened before…**

After Blair found out about Serena and Nate, Serena leaves.

Blair and Nate's relationship is rocky

Dean is from a high-class family in England, his grandparents are friends with Blair's and so are their parents.

Dean and his girlfriend, Lo had a fight and she left for New York. He is coming to New York to win her back.

Blair and Dean have met once when Blair was 14, and kept a very bad impression of each other.

Blair is Nathan's cousin and they are very close. (Eleanor is Deb and Cooper's sister)

Nathan is best friends with Dean.

The Scotts family (Nathan Haley and Jamie) are planning a trip to New York.

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New York City, New York

Last Day of School

Blair Waldorf sat on a wooden bench in posture and perfectly, waiting for her lifetime on-and-off boyfriend, Nate, infront of prestigious Constance Billiards School. She was absolutely perfect: beautiful, rich and smart. She seemed to have a life of every girl's dream. But if you look closely, behind that faultless face, there were not even a single hint of smile.

As she began to think about how her bestfriend, Serena and how she misses her, Nate appeared through St. Jude's door with hundreds of other boys. He was way more than noticeable, his green eyes stood out of the crowd, his rough hair was nowhere near _rough_, and his body seemed like it was made from a computer.He was just the perfect boyfriend, _her _perfect boyfriend and she's not going to lose him.

Nate noticed Blair, and started walking towards her.

"Hey, sweetheart how was your day?" Blair said, trying to start a conversation, which she barely ever had with him since Serena left.

"It was pretty okay." Nate replied. He tried to fix things with Blair, but everytime he thinks of Serena, he knew there was no place for Blair.

"Well, it's holiday. Any plans?" Blair asked.

"No, I guess I'll be staying here." Nate said in his broody, sad voice.

He can see Blair almost crying, she was breaking, but all he can think was about Serena.

"Nate, please. I'm trying to fix everything, but you are not trying at all. Atleast, talk to me. I love you, and I need you to tell me everything, tell me everything that has happen in your life. The happy ones, the sad ones. I'm here for you."

Nate didn't know what to say, all along, he wished that it was Serena who was saying that. But he knew that she didn't love him. She was drunk when they did _it_. She left because she wants to make things right between Blair and him. She loves Blair, not him.

"I'm sorry Blair, I'm just not ready"

"Well, there's nothing clearer than that is there?" Blair said in her small soulless tone and walked away.

She did not cry at all, she was just broken, too broken to cry.

Xxxxxxxxxxxxxxxxx

London, England

2 O'clock in the morning, Dean was sitting in his bedroom, watching TV. He was waiting for Lo, his girlfriend to come back from work. She was the one for him, she changed him. He used to be shelled and protective over his feelings, but she changed him. He began to think about their relationship. It used to be great, but now Lo is always working. She leaves very early in the morning and comes back very late in the night. They don't even have time to talk. Suddenly, Lo opened the door and walks in, she was surprised to see Dean waiting.

"Hey, I thought you were sleeping." Lo started.

"Hey Lo, can we talk for the whole night like we used to? I miss it. I miss you." Dean said.

"Dean, I have to tell you something. I'm going to New York" Lo said.

"For a holiday? That's great. I'll go with you. You actually need a break." Dean said.

"No, Dean. I'm leaving for New York. I'm going, for good. And you, you need to stay here, you belong here."

"What? Why? Don't you love me? We used to be happy."

"Dean, I'm sorry. I still love you, but I got a job promotion. It's my life Dean, I hope you understand." Lo sadly said, "I need to go. Now. Bye, my love."

At this point, she was bursting out with tears. And before Dean could say anything, she ran out the door. Now, he felt lifeless. She was the life in him. She made him smile. And first time in 'god knows how long', he cried. Yes, he cried. Dean Winchester, known for the most soulless person on earth, was sobbing for a girl.

He was not going to lose her. He was not going to lose his life. He was going to get her back, from New York.

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Tree Hill, North Carolina

At the Scotts house, Haley was chasing around with Jamie, to get him to change into his pajamas. Nathan, on the other side was in the kitchen. He was checking over the plane tickets and the passports.

"Jimmy Jam, mama's coming for you. Aaaaahhh," Haley laughed, as she slided over the couch in the living room and crashed lightly into Jamie.

"Mama, nooo. Mama got me." Jamie pouted.

"Haa! Now you have to change in to your Spiderman PJs and go to sleep. We're going to New York tomorrow!!" Haley said sounding excited.

"No, mama. I don't want to go to New York tomorrow. I want to go now. I want to see aunt Blair." Jamie continued pouting.

"Jamie," Haley started, "go to bed, we'll go to New York tomorrow".

"But mama, I want to go now!!!" Jamie begged.

Nathan saw what was happening and couldn't help, but to join the sweet conversation between his wife and his son.

"Jimmy Jam, do what your mother says. We'll see aunt Blair tomorrow."

"James Lucas Scott, you can go to New York now, but me and daddy's not going until tomorrow. So see you." Haley waved and started to walk away, smiling.

"Fine mama. I'll go with you tomorrow." Jamie said knowing that he had lost to his mum this time.

Xxxxxxxxxxxxxxxx

**Chapter 2 – What ever happened, really happened**

After Jamie was tucked in bed, Haley came downstairs and walked into the kitchen.

"Oh Haley, I have something to tell you. I just called Blair now, I said we're coming tomorrow. She's so excited to see Jamie." Nathan said.

"Oh, that's great." Haley said.

"But the thing is, Blair's in a tough time, her best friend left and now she broke up with her boyfriend. I think we should help her get through it. She's like my sister. I mean you could take her out and do like, stuff you girls do." Nathan sounded worried about his cousin.

"That sounds great, but I have a better idea. You know how we actually need to spend time alone right, as a couple." Haley started to realise her idea was amazing.

"What are you actually suggesting, wife" Nathan asked.

"I was thinking if we could spend sometime alone and leave Jamie with Blair for something like two weeks. I think Jamie would help her a lot. Oh, and cut off the 'wife' thing, it sound horrible" Haley said.

"That is actually a good idea, but are you sure? I mean Jamie is a bit, umm… Jamie" Nathan said a bit worried.

"Don't worry hun, it'll be fine. He's a good boy. He'll take care of Blair." Haley finishes off.

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The next morning Dean arrives at the airport. As soon as he landed, he dialled Lo's cell.

"Hello Dean." Lo said.

"Lo, we need to talk. I'm in New York. I want to see you."

"What? You're in New York?" Lo was shocked.

"Lo, I just need a talk. I need to ask you something in person. One last conversation and I'll leave like you want me to."

"Okay, meet me at The Palace hotel in half an hour." Lo replied and hung up.

Xxxxxxxxxxxxxxxx

Haley, Nathan and Jamie arrived at the airport as well. Haley and Nathan told Jamie about staying with Blair already and he was very excited.

"Daddy, when am I going to see aunt Blair?" Jamie asked.

"We'll get lunch at The Palace first, then we'll go see Blair" Nathan answered his son, who, by now, is too excited.

"Are we actually going to a real palace, Daddy?" Jamie asked looking confused.

"No baby, it's a hotel called The Palace" Haley answered her son.

"Ooh, that's cool." Jamie said, understandingly.

Xxxxxxxxxxxxxxxxxx

Dean arrived at The Palace and seconds later Lo walked in.

"Hi, Dean. What did you want to say? I have to go." Lo rushed.

"I need to know if you still love me and why did you leave me. You don't have to lie." Dean replied.

"Dean, I do love you and I always will, but I have to leave. I told you, I got a promotion and…"

As Lo began to explain to Dean, a guy in a white polo shirt walked in. He was big and tough, and he was walking towards them.

"Lo, you said 5 minutes, we need to go to the check the place for our wedding, the hotel called, they're waiting." The guy said.

Dean immediately grew hot. His girlfriend cheated on him. It should have been clear long ago if didn't trust her. Now, he was back into the same Dean Winchester. He was going to kill that guy.

"Hey, that's my girlfriend!!!" Dean shouted as he hit the guy.

Lo screamed. The guy stood up, he was big, he probably did felt that, Dean was strong and tough, but this guy was big. The next thing everyone saw was Dean thrown on a glass table.

Xxxxxxxxxxxxxxx

**Chapter 3 - They met, but they hope they hadn't**

As Nathan, Haley and Jamie walked into the Palace. They here people shouting and guards ran into the restaurant. Nathan told Haley to look after Jamie, while he goes to see what's happening. Nathan ran into the crowd and saw a face he hadn't seen for a year. His best friend, Dean Winchester, covered in blood.

The guard now got control of the situation and asked the guy to leave. Lo was nowhere to be seen and Dean noticed Nathan. His nose and mouth were bleeding and his arm was badly cut by a piece of glass from the table.

"Dude, are you okay? What are you doing here???" Nathan asked Dean, while helping him to get up.

"Man, get me out of here." Dean said, not answering Nathan's question.

Haley and Jamie rushed in.

"Are you okay? I think we should go to Blair's" Haley suggested.

"Yeah, are you okay, uncle Dean? I think we should go to aunt Blair's" Jamie copied his mom. Dean couldn't help but laughed.

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At the same time, Blair was also waiting for Nathan. She loved her cousin. In fact, he was her only cousin. He was like her older brother. And she was also waiting to see Jamie. Last time she saw him was when he was 2, she misses her nephew.

The lift bell rang, Blair jumped up as she saw the lift open and stood there, Dean Winchester in blood with the Scotts.

How could she react? She hated him, but it was years ago. He's in blood, should she help him. Should she be happy that she saw her cousin. She was lost and conquered by the past.

"Oh my god. What happened?" Blair rushed to the lift and helped Dean out. She took him to the sofa with Nathan supporting him. Dean was laid down.

"Marie!" Blair called for her maid. "Would you please help Dean please?". The maid ran in and started to take care Dean.

"Aunt Blair!!!!!!" Jamie screamed into the living room.

"Jamie!!!" Blair ran to Jamie and hugged him like he was her own son.

"Aunt Blair, guess what. I'm staying with you for two weeks while mama and daddy go and do their thing." Jamie shot the words out.

Blair was shocked, happy, but shocked. "Really, did they said that?" She said while turning around to look at Nathan and Haley, who are both nodding. She smiled.

"Well then, Jamie, you go upstairs with mama to unpack and change, while the adults talk, okay?" Haley asked her son.

Jamie nodded.

Xxxxxxxxxxxxxxx

Dean was now wrapped in bandages and sitting there. Blair turned to Nathan and hugged him.

"So, Nathan. Are you actually leaving your clone with me?" Blair asked smiling.

"Yeah, Haley and I thought it would be best for you to hang around with 'my clone' after all those things that happened to you." Nathan smiled.

"Well, yeah. It's a good idea. I love it. And you know you and Haley need some time alone too." Blair said, punching Nathan in the arm lightly.

This was the other side of Blair. There were no signs of the queen bee in her. She was in love and loved. With her family of course.

Nathan turned to look at Dean.

"Man, how are you? What happened back then" Nathan asked.

"I'm fine and nothing happened, okay?" Dean said starting to sound pissed.

"Do you have a place to stay? You cannot fly back to England like this." Nathan asked again worriedly. He knew that there was something going on, but he respected Dean.

"No." Dean said. It was plain and simple answer, but it was where hated Dean. The arrogance part.

"Well then. Blair, can Dean stay here for a while? Until he is better?" Nathan begged playfully, and Blair could not object. In reality, if she was the queen bee, Dean would actually go down the rubbish bin by now.

"Okay, sure." Was all Blair said, staring at Dean.

Dean sensed the unfriendliness in her tone. He hated that about her. She was always judging people, sorting them out and being too forward about people. She was clearly annoyance to him.

"Oh, by the way. Where's aunt Eleanor?" Nathan asked.

"She's in Paris. Work." Blair said half sarcastically tone.

"Yup, and the guy is changed" Haley said, piggy-backing Jamie down the stairs.

"Oh yeah. Should we go Haley? I think the limo's here." Nathan said.

"Yeah, we should. Bye Dean, Bye Blair, Bye Jimmy Jam" Haley said hugging Blair and Jamie.

"Bye." Nathan said, before leaving with Haley.

Xxxxxxxxxxxxxx

**Chapter 4 – There were lots more, but its down to three**

"Jamie, what do you want to do?" Blair asked Jamie.

"I don't know. What do you want to do, aunt Blair?" Jamie copied his aunt.

"I don't know, darling." Blair said.

"And what do you want to do, uncle Dean?" Jamie asked.

Dean was surprised. "I don't know too." Dean said. Blair turned and glared at him.

"Aunt Blair, I'm hungry. Let's go out to eat. Uncle Dean's coming too." Jamie said.

"What? I haven't said anything yet, James." Dean laughed at his bestfriend's son.

"Well, you have to come. I'm dragging you to the restaurant." Jamie replied.

"Okay, we'll go for lunch. Uncle Dean doesn't want to come, so we'll leave him here, is that alright?" Blair asked and stared at Dean, who stared back also.

Jamie nodded.

"No, no. Don't worry. I'll go. Who wants to let down Jamie Scott anyways, right?" Dean said jokingly to Jamie.

Jamie laughed and Blair did not look pleased, but she pretend to put on the smile to her nephew.

Xxxxxxxxxxxxxxx

Blair's POV

Oh my god, oh my god, oh my god. This bastard is killing me. Yes, he is injured, but I'm actually going to injure him more. Damn him. I should have never let him stay. Now, we're having lunch together, with a child. What would Gossip Girl say about that? It's all on Nathan. Dean Winchester, such an arrogant bastard. A hot bastard!

Errrrrgh! 'Hot bastard???' What the hell was I thinking? But he's really hot! Blair Cornelia Waldorf shut the hell up!!! he's staring at you, say something. Jamie's not here, say anything.

"What are you looking at?" I asked.

"Nothing." He said.

I saw it, he was looking, I swear he was looking, how come he said 'nothing'. Say something smart, say it!

"Liar", there I said it. Ha! Now he doesn't have anything to say. I'll just give him a big 'L'. Uh oh! Too late, Jamie's back from the bathroom.

"You okay Jamie?" I asked my nephew.

"Yep, aunt Blair." He said in his cute voice.

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Dean's POV

Damn it! She's so annoying. She made a big deal on me looking at her. What's wrong with that? And why did I look at her in the first place? Now the problem is what's wrong with me. I just got dumped! This is so wrong.

"I have to go to the bathroom, Jamie," she said in her fake sweet voice.

"Okay, aunt Blair." He replied.

Such a cute kid. I wish I could reproduce like Nathan. Blair stood up and walked off.

Oh my effing god. Look at that ass….

Dean Winchester, NO!!! Stop it. She's a total 'b' and she thinks you're nothing. Don't dream! Stop dreaming! Jamie's looking, you're acting weird. Dean, cut it off!

Xxxxxxxxxxxxxxx

Jamie's POV

Uncle Dean is so weird. He was staring at aunt Blair for so long and making funny faces. He's so funny. Should I ask him what's wrong? Yeah, mama and daddy is not here. I'm not going to get told off.

"Uncle Dean, are you okay? You're staring at aunt Blair and you're making funny faces. You're funny." I said and laughed.

Later, we talked about basketball and daddy, before aunt Blair came back. I'm going to tell her about uncle Dean's weird face. It's so funny. She's going to like it.

"Aunt Blair, just now uncle Dean was staring at you and he's made funny faces. It's so funny!" I said happily.

Now it's even funnier. Both aunt Blair and uncle Dean's making funny faces at the same time. I started to laugh so badly.

"Hahaha, you guys are both doing funny faces…" I laughed out.

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**Chapter 5 – I hate you, but I have to pretend I don't**

Later that night, when Jamie was tucked into bed, Blair came downstairs to get herself warm milk in the kitchen. It was dark downstairs, so she switched the kitchen lights on, only to find Dean sitting with a plate of chocolate cake too.

"Didn't know you hunt in the night as well, Blair" he coughed, but it was clear to her.

"Well, I was just checking if you are the hunting type too." Blair came up with an excuse.

"So you care about me, do you?" Dean asked sarcastically with half a smirk.

"You wish. It'll be the last thing on earth I'll ever do: to care for a self-possessed ass" Blair shot back.

"Then I guess, you have done everything on earth already. Ready to do stuff in space?" Dean replied immediately.

"Does that include getting hit by a stranger, because you can't deal with your own problems?" Blair said furiously.

"That's not your business Waldorf." Dean said, getting angrier than Blair.

Blair did not gave up.

"Then why does it end up on you staying here, in my house!" she shouted.

"It's called kindness, Blair, something you'll never understand. You're always the same, five years ago or now." Dean said in his famous heartless tone.

"And same to you, Dean. Always arrogant and too proud. You can't even let anyone in, including yourself. You can't feel, can't you? You don't know what it's like to be someone else." Blair was now fuming.

"And you think you know me?" Dean asked back.

Blair now heard footsteps coming down the steps. She knew it was Jamie. She was afraid that he heard the argument and was scared of her.

"Aunt Blair, Uncle Dean, I can't go to sleep. Can we watch TV?" Jamie begged.

"Yeah, of course, J, why not?" Dean answered, knowing that Blair was looking at him fiercely.

"Can you guys watch it with me?" Jamie asked again.

"Yup, sure, Jamie." Blair blurted in this time. Dean agreed to watch TV with Jamie and Blair.

"Aunt Blair, uncle Dean." Jamie started. Blair and Dean both turned, "Do you know you guys look like mama and daddy."

"Really? I don't understand Jamie. Can you explain to me please?" Dean acted dumb. He knew what Jamie meant, but he likes it when Blair looks annoyed.

"I mean you guys look married. Do you guys love each other?"

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End file.
